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N-(3-azolylphenyl) isonicotinamide compounds as well as preparation method and application thereof

A technology of azolyl phenyl and isonicotinamide is applied in the field of medicine to achieve the effects of high yield, improved activity and easy mass production

Inactive Publication Date: 2018-12-14
中国医科大学
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because the cyano group of this series of compounds fails to combine with the Asn768 residue, although the activity of this series of compounds is better than that of allopurinol, it is an order of magnitude lower than that of topirastat

Method used

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  • N-(3-azolylphenyl) isonicotinamide compounds as well as preparation method and application thereof
  • N-(3-azolylphenyl) isonicotinamide compounds as well as preparation method and application thereof
  • N-(3-azolylphenyl) isonicotinamide compounds as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Preparation of 4-nitro-2-(1H-tetrazol-1-yl)phenol

[0061] Add 2-amino-4-nitrophenol (10.0g, 64.88mmol), glacial acetic acid (100mL) and triethyl orthoformate (20.7g, 129.67mmol) into a 500mL reaction flask, slowly add sodium azide under stirring (8.4g, 129.67mmol), react overnight at 80°C. Cool after the reaction, pour into ice water, filter with suction, wash the filter cake with plenty of water, and dry naturally to obtain 11.7 g of reddish-brown solid, yield: 87.1%.

Embodiment 2

[0063] Preparation of 4-amino-2-(1H-tetrazol-1-yl)phenol

[0064] Add 4-nitro-2-(1H-tetrazol-1-yl)phenol (6.0g, 28.96mmol), reduced iron powder (6.5g, 115.84mmol), ammonium chloride (3.1g ,57.92mmol), ethanol (90mL) and water (30mL), reflux at 80°C overnight, the reaction was complete, diluted with water, extracted with ethyl acetate (50mL*3), washed with saturated brine, dried over anhydrous sodium sulfate, filtered, Concentrate under reduced pressure to dryness to obtain 4.24 g of refined product, yield: 82.6%.

Embodiment 3

[0066] Preparation of 4-isonicotinamide-2-(1H-tetrazol-1-yl)phenylisonicotinic acid methyl ester

[0067] Add 4-amino-2-(1H-tetrazol-1-yl)phenol (1.0g, 5.64mmol), triethylamine (5.2g, 50.76mmol) and dichloromethane (20mL) in 250mL reaction flask,- Add dichloromethane (20mL) and isonicotinic acid chloride (4.02g, 22.56mmol) dropwise under stirring at 5°C. After maintaining the temperature for 1 hour, add water, separate the organic layer, extract the aqueous layer with dichloromethane, and combine the organic layers. Wash with saturated brine, dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to dryness to obtain 1.74 g of refined product, yield: 79.4%.

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Abstract

The invention belongs to the field of medicine, and relates to N-(3-azolylphenyl) isonicotinamide compounds as well as a composition comprising the same and a preparation method of the N-(3-azolylphenyl) isonicotinamide compounds. The invention further relates to the application of the compounds and the compositions in anti-gout. The compounds have a general formula I as shown in the specification; the molecular structure of the compounds is more innovative and the activity is greatly enhanced. Moreover, the compounds with the general formula I provided by the invention are simple and feasiblein preparation method, high in yield and easy to be mass-produced.

Description

technical field [0001] The invention belongs to the field of medicine, and relates to an N-(3-azolylphenyl)isonicotinamide compound, a composition containing the compound and a preparation method thereof. The present invention also relates to the application of these compounds and compositions in anti-gout. Background technique [0002] Gout is a group of heterogeneous metabolic diseases caused by long-term hyperuricemia (Hyperuricemia) leading to urate deposition in joints and soft tissues. Its clinical characteristics are: hyperuricemia, acute and chronic arthritis, joint deformity, chronic interstitial nephritis and renal nodules, etc. In severe cases, renal failure and cardiovascular and cerebrovascular diseases may also be life-threatening. According to statistics, gout has become the second largest metabolic disease after diabetes. In recent years, with the improvement of people's living standards and the change of diet structure, the incidence of gout in my country ...

Claims

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Application Information

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IPC IPC(8): C07D401/12A61K31/4439A61P19/06
CPCA61P19/06C07D401/12
Inventor 孟繁浩张廷剑张毅李松晔
Owner 中国医科大学
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